The Best to Ever Grace the Oscar’s Red Carpet

Some people watch the Academy Awards to see the Best Films, the stage performances, the host of the show, and of course, the winners. And then there are those who watch the Oscars solely to see what the glamorous celebrities are wearing – Who Wore it Best? The red carpet is known for showcasing Hollywood’s most celebrated stars as well as the fashion designers. As you probably have heard on any pre-awards show on the red carpet, the number one question the celebs are asked is “Who are you wearing?”

Well, we would like to take a trip down memory lane and look at the best dressed and the less-best dressed celebrities that walked down the carpet. There are definite hits and misses which can only remind us that, like us, celebrities make fashion mistakes too! Only they have millions of eyes on them and photos that will be eternally traceable. But that’s part of the package of being rich and famous.

So let’s start with those from the 91st Academy Awards.

Lady Gaga – The Lady of the Night

Although Lady Gaga didn’t win the Best Actress award for her role in A Star is Born, she still managed to steal the show on the red carpet at the 91st Academy Awards. She epitomized glamor with her gown by Alexander McQueen.


She even paired it with Tiffany’s 128-carat yellow diamond necklace. The necklace was last seen worn by Audrey Hepburn at a “Breakfast at Tiffany’s” photoshoot. Talk about style and class!

Emma Stone – Always Elegant

Best supporting actress nominee Emma Stone wore a breathtaking gold and copper gown by Louis Vuitton. She may have gotten some remarks about the unique dress, but all in all, it was a real stunner!


The exaggerated sleeves and the texture made Emma’s dress one to remember from a flooded red carpet.

See the next much-loved dress from the Hollywood star-studded red carpet!

Amy Adams – Art Deco Queen

Amy Adam was also up for Best supporting actress for her role in Vice. And she showed up on the red carpet with a figure-hugging white gown with silvery accents.


Her dress was designed by Versace, a favorite among red carpet celebrities. Her dress can be categorized in the art deco style.

Regina King – Took Home an Oscar

Regina King took home an Oscar for Best supporting actress for her role in If Beale Street Could Talk. She kept it simple with a less is more approach and wore a gorgeous chic white dress.


Her strapless Oscar de la Renta gown was a classic choice and was a perfect choice for having all eyes on her when she said her speech on stage.

Next, a “Crazy Rich Asian” had a stellar look on the red carpet!

Gemma Chan – One “Crazy Rich Asian”!

The “Crazy Rich Asians” star, Gemma Chan followed suit this year with all the pink that embraced the red carpet at the Oscars.


She came wearing a voluminous pink, high-collared dress by Valentino. While it’s really fluffy and big, she pulled it off well!

Jennifer Lopez – A Mosaic of Mirrors

Jennifer Lopez was a presenter at the awards show and she caught everyone’s stares with her mirrored dress by designer Tom Ford. Can you blame them? Her gown is literally eye-catching!

Source: David Fisher/REX/Shutterstock.

The long-sleeved, mirror embroidered gown will go down as one of J-Lo’s best – and she has pulled off many red carpet winners over the years!

Next, a rather surprising look for a male star!

Billy Porter – Striking a Pose

Billy Porter, star of “Pose,” was one of the first to enter the red carpet and is unsurprisingly one of the most talked about in terms of his fashion choice for the night.

Source: Twitter

As you can see, he’s wearing a unique black velvet tux dress, and it was designed by Christian Siriano. The designer tweeted the photo, saying it was an “honor to create this moment.”

Linda Cardellini – Dropping Jaws

There’s always going to be jaw-dropping moments on the red carpet. So it would be incomplete not to show a few of the strange fashion choices of the night.

Source: Invision/AP/Richard Shotwell

Green Book actress Linda Cardellini stole the show with her uncomfortable mix of both hot pink ruffles and the “mullet” hemline. Risky and bold!

The next memorable dress is another pink moment on the red carpet!

Sarah Paulson – We Don’t Get It

Sarah Paulson, the Ocean’s 8 star, has usually been a spot-on kind of star when it comes to her style. But this is a rather alarming curveball.

Source: Invision/AP/Richard Shotwell

We don’t understand why she chose this pink ensemble. It’s confusing, but we’ll forgive her!

Rachel Weisz – We’re on the Fence

Rachel Weisz was up for Best Supporting Actress for her part in The Favourite. She wore a rather unusual dress that is amazingly both beautiful and ugly at the same time. Which is why we’re undecided.

Photo by Jeff Kravitz/FilmMagic

It’s half raincoat, half classy gown. Although it’s a bit puzzling, we applaud her for daring to be different!

Next, the right amount of drama!

Marina de Tavira – Looking Lovely

Best Supporting Actress nominee Marina de Tavira, recognized for her role in Roma, was also noticed for her lovely dress that night.


Her dress was truly breathtaking and a reminder that a dramatic look doesn’t have to be too much to handle. This was the perfect amount of drama.

Brie Larson – A Silver Goddess

The young actress showed up on the red carpet in a sparkling, high neck silver halter gown with a thigh-high slit. Not everyone can pull off a look like that.

Source: Christopher Polk/REX/Shutterstock

The Captain Marvel star presented an award this time.

Amandla Stenberg – A Starlet from the 20s

The 20-year-old actress joined the Hollywood Giants at the 2019 Academy Awards wearing an incredible nude and silver fringe-covered dress.

Source: David Fisher/Shutterstock

Her gown was a ’20s-inspired Miu Miu design. She would have fit right in at one of Gatsby’s parties.

Let’s give the list a refresher and show some of more memorably dressed men on the red carpet!

Spike Lee – A Purple Kinda Night

Director Spike Lee showed up in Jordan sneakers with a Jaeger-LeCoultre watch and a very eye-catching purple suit. Why? Well, why not?

Source: Robert Gauthier / Los Angeles Times

He was up for Best Director for his film Blackkklansman. He didn’t win, but he’ll definitely be remembered for this outfit.

Rami Malek – The Classic Winner

The big winner of the night was Rami Malek who won Best Actor for his part in Bohemian Rhapsody. He kept it classic with a Saint Laurent by Anthony Vaccarello tuxedo and a Cartier watch.

Source: AAP

There’s nothing classier than a black tuxedo. And it’s exactly what an Oscar-winning actor should wear.

Next – the Game of Thrones star showed up in a rather unmanly color.

Jason Momoa – Hollywood’s Trendsetter

The biggest star in Hollywood came in a pink velvet tux by Fendi, look as remarkable as always.

Source: Robert Hanashiro-USA TODAY NETWORK

The actor has swagger – he just can’t help it. And his matching scrunchie on his wrist shows how confident he is in his masculinity!

Stephan James – Red Velvet Style

The star from If Beale Street Could Talk appeared on the red carpet in a striking red velvet suit and white boots.

Source: Jordan Strauss/Invision/AP/REX/Shutterstock

The young Canadian actor looks like he’s an up and coming actor in the Hollywood scene. You’ll see more of him that’s for sure.

Halle Berry Wowed us in 2002

Remember Halle Berry at the 2002 Academy Awards? We all do. Her dress, by Elie Saab, was completely unique. With a satin train and embroidery in the essential places, she wowed all the red carpet onlookers.


That evening, she won Best Actress Oscar for her performance in Monsters Ball. Berry was the first African-American actress to win the award, and so her emotional speech was understandable and well deserved!

Kate Hudson Was a Vintage Beauty in 2003

Kate Hudson wore this stunning vintage Versace gown. The delicate, intricate design took 500 hours to create! It’s made of hand-made gold chiffon silk.


And she completed the look with the perfect hair, makeup and jewelry.

Audrey Hepburn, Forever Elegant in 1954

Audrey Hepburn wore Hubert de Givenchy for the 1954 Oscars and she was the epitome of classic Hollywood elegance. She won the Best Actress award for Roman Holiday that night.


Givenchy was apparently her favorite designer after this night, as it was her first time that she wore the designer off-screen. She must have felt that he gave her good luck.

Hilary Swank, a Deep Blue Goddess in 2005

Hilary Swank won Best Actress in 2005 wearing a Guy Laroche gown made of 27 yards of silk jersey. The front of the dress looked deceivingly modest, but the back featured a very low-skimming cut.


She must have known she was going to win wearing a gown like that!

Sophia Loren – Glamorous in 1958

Sophia Loren knew how to dress to show off her curves, like this satin floral dress that she wore to the 1958 Academy Awards.


Her diamond earrings and necklace make the glamorous look all that more complete.

Charlize Theron, Staying Classy in 2004

Charlize Theron showed up to the 2004 Oscars wearing a rather simple yet breathtaking white Gucci dress, proving that sometimes less is more.

Source: pinterest

She won an award that night for Best Actress for her role in Monster. It’s amazing to see how remarkable different she looks in comparison to her character in the movie.

Michelle Williams, Strutting Yellow so Elegantly in 2006

While there was a debate over Michelle Williams’ Vera Wang dress at the 2006 Oscars, we absolutely love it. The canary yellow was a refreshing look for a typically dim red carpet.

Source: pinterest

She had a pretty much equal number of best-dressed and worst-dressed votes on this one. But we applaud her courage in standing out amongst the rest.

Daryl Hannah, Sporting the White Gloves in 1988

Elbow-length gloves were starting to drop in their popularity at the time, which is why Darryl Hannah’s appearance at the 1988 Academy Awards was even more notable.

Photo by commercial photographer Michael Grecco

The white gloves along with her glamorous gold dress and silky blonde hair made her look flawless and classy as ever.

Penelope Cruz in a Look to Remember in 2007

Penelope didn’t score an Oscar that night but she did win praise for her choice of what to wear. She wore a beautiful blush colored gown by Versace.

Source: Bauer Griffin

Her entrance onto the red carpet was memorable and her dress remains on the best-dressed list of all time.

Nicole Kidman in Scarlet Red at the 2007 Academy Awards

How is it that Nicole Kidman always manages to pull off an extremely elegant look? As she floated down the red carpet that night, everyone’s eyes were on her. Can you blame them with a color like that?

Source: popsugar

She was wearing a Balenciaga gown, with a large bow that trailed forever behind her, adding an extra bit of drama to her already dramatic gown.

Emma Stone, Rocking Vintage in 2016

Emma won her Oscar for La La Land that night and won everyone’s hearts in the fashion department as well.


Her vintage Givenchy Haute Couture dress was the perfect thing to wear for an award-winning night and the Oscar was the perfect accessory.

Charlize Theron – A Look to Forget in 2010

Because she has had so many more hits than misses on the red carpet, we (and everyone who was watching) will forgive her for this regrettable choice.


It’s okay Charlize, you’re only human and humans make mistakes and it doesn’t make any dent on the fabulous person that you are! But wow, what a dress…

Bjork, Making a Statement in 2001

Bjork’s was probably one of the most famous Oscars dresses of all time. But for the wrong reasons. It’s not clear why she chose to wear a fake swan too-too dress.


But there must have been people in her circle that warned her about this decision. Obviously, she didn’t listen.

Hillary Swank, Looking a Lot Younger in 2003

We wouldn’t be surprised if her choice of gown was actually made by a 7-year-old girl (maybe a niece?). This dress at the 2003 Academy Awards was unsurprisingly on the worst-dressed list.


We only have one question for Hillary: What happened?

Barbara Streisand Caused a Commotion in 1969

Barbra Streisand won the best actress for her starring role in Funny Girl at the 1969 Academy Awards.

Source: Bettmann/Corbis

But that night she also won the unofficial award for the most scandalously clad, wearing this sheer mod Arnold Scaasi dress. But it’s Barbara Streisand – she does what she wants.

Celine Dion, 1999

Celine Dion has a way of being very random. She showed up to the red carpet in 1999 wearing a suit. But not a regular suit – a backward suit!

Source: pinterest

And not just a backward suit. A matching hat! And then she added some sunglasses to complete the look. We don’t understand, but we think she’s brave and we like that.

Uma Thurman, a Messy Mistake in 2004

Who knows why Uma chose this messy white dress by Christian Lacroix for the 2004 Oscars. Chances are, she regretted it afterward.


Her look won her the unofficial title of “Swiss Miss.”

Whoopi Goldberg at the 1993 Academy Awards

Whoopi left everyone with a loss for words at the 1993 Oscars. Everything from the costume-design-ish style to the choice of colors left everyone speechless.


Whoopi has always been an outspoken comedian and actress, and her fashion also had a lot to say.

Geena Davis in an Unusual Dress at the 1992 Oscars

Geena appeared on the red carpet in 1992 wearing this. We don’t even have sufficient words to describe whatever this is supposed to be.


Cher – We Have No Words

Cher was notorious for showing up and shocking the crowd. And here she was at the 1986 Oscars, looking as scandalous as ever.


Next, even stars like Angelina Jolie make very strange mistakes.

Angelina Jolie – Inspired by Vampires

Angelina Jolie must have just watched her ex-husband’s Interview with the Vampire before choosing this dress for the 2000 Academy Awards.

Source: Kevin Mazur/

She got the Oscar for her role in Girl, Interrupted.

Lizzy Gardiner – A Walking Advertisement

The actress shocked the crowds when she wore a dress made out of American Express Gold Cards to the 1995 Oscars.

Source: Pinterest

This dress was clearly supposed to make a statement; we just don’t know what that statement was supposed to be.